Dimethyl Sulfoxide → 2',6'-Dimethyl-4'-(3-(methylsulfonyl)propoxy)biphenyl-3-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

2-Bromo-1,3-dimethyl-5-[3-(methylsulfonyl)propoxy]benzene (250.0 g), 3-formylphenylboronic acid (122.5 g), tripotassium phosphate (330.4 g), 10% palladium carbon 50% water-containing product (12.5 g) and 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (5.5 g) were added to dimethyl sulfoxide (2500 mL) and water (1250 mL). After deaeration and nitrogen substitution, the mixture was heated, and stirred at 80° C. for 3 hr. The reaction mixture was left standing, and the oil component in the lower layer was removed. The mixture was cooled, ethyl acetate (875 mL) was added, and the mixture was stirred. The insoluble material was removed by filtration, and washed with ethyl acetate (625 mL). To the filtrate was added 10% brine (1500 mL), the mixture was stirred, and the organic layer was separated. The aqueous layer was extracted again with ethyl acetate (1500 mL). The organic layers were combined, and washed twice with 10% brine (1500 mL). The organic layer was concentrated to 750 mL, ethyl acetate (1500 mL) was added, and an operation to concentrate the mixture to 750 mL again was performed twice. To the concentrate were added ethyl acetate (1250 mL) and activated carbon (25 g), and the mixture was stirred at room temperature for 30 min. The insoluble material was removed by filtration, and washed with ethyl acetate (750 mL). The filtrate was concentrated to 750 mL under reduced pressure, and stirred at room temperature overnight. Normal heptane (3750 mL) was added dropwise, and the mixture was stirred at room temperature for 2 hr. The precipitated solid was collected by filtration, and the solid was washed with a mixture (750 mL) of ethyl acetate.normal heptane (1:5), and dried under reduced pressure to give 2′,6′-dimethyl-4′-[3-(methylsulfonyl)propoxy]biphenyl-3-carbaldehyde (235.0 g).

Provenance & Evidence